In the wake of North Korea’s progressive missile testing that set even the usually stoic Japanese people into a panic mode, Japan has found itself at the mercy of its former enemies. In an ironic twist of fate, Tokyo’s security outlooks seem to have become hostage to the strategic calculations of its fiercest nemesis in the past. This paper asks whether Prime Minister Shinzo Abe’s desire for constitutional change is precipitated mainly by the resurgence of Japanese nationalist sentiments as what many of his critics claim, or if there are genuinely rational justifications for revising the country’s 72-year old Constitution. And if so, why has it been so elusive for many Japanese leaders? Using neoclassical realism theory, I analyze the structural contexts and domestic intervening variables that simultaneously drive and prevent the realization of constitutional change in Japan. I argue that state leaders like Abe and those who have come before him have always been prone to acquiring flawed and inaccurate perceptions of the systemic stimuli; susceptible to making irrational and unsound decisions; and ineffective at mobilizing the national resources demanded by their preferred policies and strategies. Thus, despite having rational justifications, the quest for constitutional change has remained elusive for many Japanese leaders. Success will require Abe to carefully harmonize domestic and international expectations; prudently balance Japan’s benign security intentions and hawkish military strategies; and shift away from his pragmatic–ambivalent style of domestic politics.